title: Highly enantioselective oxidation of phenyl methyl sulfide and its derivatives into optically pure (S)-sulfoxides with Rhodococcus sp. CCZU10-1 in an n-octane-water biphasic system.
abstract: Enantiopure sulfoxides can be prepared via the asymmetric oxidation of sulfides using sulfide monooxygenases. The n-octane-water biphasic system was chosen for the bio-oxidation of a water-insoluble phenyl methyl sulfide (PMS) by Rhodococcus sp. CCZU10-1. In this n-octane-water system, the optimum reaction conditions were obtained. (S)-phenyl methyl sulfoxide ((S)-PMSO) with >99.9 % enantiomeric excess formed at 55.3 mM in the n-octane-water biphasic system. Using fed-batch method, a total of 118 mM (S)-PMSO accumulated in 1-L reaction mixture after the 7th feed, and no (R)-PMSO and sulfone were detected. Moreover, Rhodococcus sp. CCZU10-1 displayed fairly good activity and enantioselectivity toward other sulfides. In conclusion, Rhodococcus sp. CCZU10-1 is a promising biocatalyst for synthesizing highly optically active sulfoxides.
authors.affiliation: Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology & College of Pharmaceutical Engineering and Life Sciences, Changzhou University, Changzhou, 213164, China, heyucai2001@163.com.
authors.forename: Yu-Cai
authors.initials: YC
authors.lastname: He
authors.forename: Cui-Luan
authors.initials: CL
authors.lastname: Ma
authors.forename: Zhen-Xing
authors.initials: ZX
authors.lastname: Yang
authors.forename: Min
authors.initials: M
authors.lastname: Zhou
authors.forename: Zhen
authors.initials: Z
authors.lastname: Xing
authors.forename: Jiang-Tao
authors.initials: JT
authors.lastname: Ma
authors.forename: Hui-Lei
authors.initials: HL
authors.lastname: Yu
mesh_terms: D001711:Biotransformation; D009795:Octanes; D010084:Oxidation-Reduction; D012240:Rhodococcus / Q000378:metabolism*; D012997:Solvents; D013237:Stereoisomerism; D013440:Sulfides / Q000378:metabolism*; D013454:Sulfoxides / Q000378:metabolism*; D014867:Water
chemical_list: D009795:Octanes; D012997:Solvents; D013440:Sulfides; D013454:Sulfoxides; D014867:Water; C093850:methylphenylsulfide; C026728:octane